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The synthesis of novel crown ethers, part ix, 3-phenyl chromenone-crown ethers

✍ Scribed by M. Bulut; Ç L. Erk

Publisher
Journal of Heterocyclic Chemistry
Year
2001
Tongue
English
Weight
51 KB
Volume
38
Category
Article
ISSN
0022-152X

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✦ Synopsis

3-Phenyl-and 3-(p-methoxyphenyl)-7,8-dihydroxy and -6,7-dihydroxychromenones were prepared from ethyl 3-oxo-2-phenylpropanoate, ethyl 3-oxo-2-(4-methoxyphenyl)-propanoate and the trihydroxy benzenes in H 2 SO 4 . 3-Aryl-7,8-and3-aryl-6,7-dihydroxy-2H-chromenones reacted with the bis-dihalides of polyglycols in DMF/MeCO 3 to afford 12-Crown-4, 15-Crown-4 and 18-Crown-6-chromenones. The products were identified with IR, 1H NMR, low and high resolution mass spectroscopy and elemental analysis. Some 1:1 cation association constants, K b , of the 3-phenyl chromenone crown ethers with Li + , Na + , K + and Rb + cations were studied by steady state emission fluorescence spectroscopy; K b chromenone-crown complexes displayed crown ether-cation binding selectivity rules properly in acetonitrile.

📜 SIMILAR VOLUMES

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The Synthesis of Anthracene Crown Ethers Derived from Benzo-Crown Ethers. -A method to obtain anthracene crown ethers starting from benzo-15-crown-5-ether and benzo-18-crown-6-ether and various aldehydes is described. The yield strictly depends on the aldehyde. Cyclohexanone leads to a new class of